Coupling reaction of 1-alkynes with alkenyl halides in the presence of (Ph3P)4Pd/CuI with PhCH2N+Et3 Cl- as phase transfer reagent gave high yields of 1,3-enynes. E.g., coupling of H2C:CMeBr with Me(CH2)4C≡CH (I) in C6H6/10% aq. NaOH gave 80% H2C:CMeC≡C(CH2)4Me. The reaction of alkynes with alkenyl halides of known configuration occurred stereospecifically. E.g., reaction of (E)-BuCH:CHI with I gave 50% (E)-BuCH:CHC≡C(CH2)4Me, exclusively. The usefulness of the reaction was shown by the prepn. of some insect sex pheromones.
Insect sex pheromones: palladium-catalyzed synthesis of aliphatic 1,3-enynes by reaction of 1-alkynes with alkenyl halides under phase transfer conditions
ROSSI, RENZO;CARPITA, ADRIANO;
1982-01-01
Abstract
Coupling reaction of 1-alkynes with alkenyl halides in the presence of (Ph3P)4Pd/CuI with PhCH2N+Et3 Cl- as phase transfer reagent gave high yields of 1,3-enynes. E.g., coupling of H2C:CMeBr with Me(CH2)4C≡CH (I) in C6H6/10% aq. NaOH gave 80% H2C:CMeC≡C(CH2)4Me. The reaction of alkynes with alkenyl halides of known configuration occurred stereospecifically. E.g., reaction of (E)-BuCH:CHI with I gave 50% (E)-BuCH:CHC≡C(CH2)4Me, exclusively. The usefulness of the reaction was shown by the prepn. of some insect sex pheromones.File in questo prodotto:
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